Glutaric Acid → HCID 178512808, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 360 mg (1.62 mmoles) of 7-guanidinoheptanamido hydrochloride, 568 mg (1.94 mmoles) of N-[4-(3-aminopropyl)aminobutyl]-2,2-dihydroxyethanamide dihydrochloride obtained in Example 4, 214 mg (1.62 mmoles) of glutaric acid, and 0.36 ml of water was heated at 60° C. for 24 hours. After completion of the reaction, 5 ml of water was added to to the reaction mixture, then passed through a column (20 mm inner diameter) packed with 150 ml of CM-Sephadex® C-25 (Na-type), and fractionated by the gradient elution with 1.5 liters of water and 1.5 liters of 0.8M aqueous sodium chloride solution. The fractions containing the desired product were combined, then concentrated, and extracted three times with 10 ml of methanol. The methanol layer was passed through a column packed with 150 ml of Sephadex® LH-20, and developed with methanol. The fractions containing the desired product were combined and evaporated to dryness, yielding 317 mg (39% yield) of white powder of N-[4-(3-aminopropyl)aminobutyl]-2-(7-guanidinoheptanamido)-2-hydroxyethanamide trihydrochloride.

Provenance & Evidence